Cryogels Based on Poly(2-oxazoline)s through Development of Bi- and Trifunctional Cross-Linkers Incorporating End Groups with Adjustable Stability

GND
1334192138
Affiliation
Laboratory of Organic Chemistry and Macromolecular Chemistry (IOMC) ,Friedrich Schiller University at Jena ,Humboldtstraße 10 ,07743 Jena ,Germany
Engel, Nora;
GND
1333881126
Affiliation
Laboratory of Organic Chemistry and Macromolecular Chemistry (IOMC) ,Friedrich Schiller University at Jena ,Humboldtstraße 10 ,07743 Jena ,Germany
Hoffmann, Tim;
GND
1328154882
ORCID
0000-0001-8286-4854
Affiliation
Laboratory of Organic Chemistry and Macromolecular Chemistry (IOMC) ,Friedrich Schiller University at Jena ,Humboldtstraße 10 ,07743 Jena ,Germany
Behrendt, Florian;
GND
1276149425
ORCID
0000-0002-4660-1691
Affiliation
Institute of Inorganic and Analytical Chemistry (IAAC) ,Friedrich Schiller University at Jena ,Humboldtstraße 8 ,07743 Jena ,Germany
Liebing, Phil;
GND
1027788505
ORCID
0000-0003-0712-5255
Affiliation
Laboratory of Organic Chemistry and Macromolecular Chemistry (IOMC) ,Friedrich Schiller University at Jena ,Humboldtstraße 10 ,07743 Jena ,Germany
Weber, Christine;
GND
123955769
ORCID
0000-0003-4210-2956
Affiliation
Laboratory of Organic Chemistry and Macromolecular Chemistry (IOMC) ,Friedrich Schiller University at Jena ,Humboldtstraße 10 ,07743 Jena ,Germany
Gottschaldt, Michael;
GND
113792077
ORCID
0000-0003-4978-4670
Affiliation
Laboratory of Organic Chemistry and Macromolecular Chemistry (IOMC) ,Friedrich Schiller University at Jena ,Humboldtstraße 10 ,07743 Jena ,Germany
Schubert, Ulrich S.

1,4-Bis­(iodomethyl)­benzene and 1,3,5-tris­(iodomethyl)­benzene were used as initiators for the cationic ring-opening polymerization (CROP) of 2-ethyl-2-oxazoline (EtOx) and its copolymerization with tert -butyl (3-(4,5-dihydrooxazol-2-yl)­propyl)­carbamate (BocOx) or methyl 3-(4,5-dihydrooxazol-2-yl)­propanoate (MestOx). Kinetic studies confirmed the applicability of these initiators. Termination with suitable nucleophiles resulted in two- and three-armed cross-linkers featuring acrylate, methacrylate, piperazine-acrylamide, and piperazine-methacrylamide as polymerizable ω-end groups. Matrix-assisted laser desorption/ionization mass spectrometry and nuclear magnetic resonance (NMR) spectroscopy confirmed the successful attachment of the respective ω-end groups at all initiation sites for every prepared cross-linkers. Except for acrylate, each ω-end group remained stable during deprotection of BocOx containing cross-linkers. The cryogels were prepared using EtOx-based cross-linkers, as confirmed by solid-state NMR spectroscopy, scanning electron microscopy, and thermogravimetric analysis. Stability tests revealed a complete dissolution of the acrylate-containing gels at pH = 14, whereas the piperazine-acrylamide-based cryogels featured excellent hydrolytic stability.

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